Jail Break (also known as The Great Escape, Pirate Prison Break, and Back in the Saddle) is a challenge that originated in Survivor: Thailand as a tribal challenge. It has also been used as a Redemption Island duel.
When used as a tribal challenge, players are locked in a makeshift jail cell and shackled. To escape, players must use the resources provided to create a long pole to retrieve three keys. These keys are to be used to unlock their shackles and they must then dig out of the cell. The first tribe to get all of their members out of the cell would win.
In the individual Redemption Island version of the challenge, players are no longer shackled. Because of this, the keys are now used to unlock the cell door. In Edge of Extinction and Winners at War, the castaways first had to climb a net and retrieve bags of sticks before working on the cell door portion of the challenge. After getting through the cell door, they then had to navigate a ball to the top of a vertical snake maze.
This challenge debuted in Survivor: Thailand. Shackled by locks, each tribe would be placed in a jail cell. Using the resources on the ground, they had to escape the cell by reaching for the keys that hung on posts outside of the cell. They would then unlock their shackles and dig out of the jail. The Chuay Gahn tribe beat Sook Jai for immunity.
In Survivor: The Amazon, in order to escape of the cage, the tribe members had to untie a series of ropes in order to release a machete. Then the tribes had to use their machete to cut through a rope, undo another series of knots in order to release a plank, which will in turn release a pole. They then used the pole to retrieve a set of keys on the outside of the cage. Once the keys were collected, they unlocked their chains and released their escape hatch. Jaburu won their second Immunity Challenge, sending Tambaqui to Tribal Council.
In Survivor: Pearl Islands, the challenge was used as the Immunity Challenge of the Outcasts twist. If The Outcasts beat one tribe, they would vote one member back into the game and the losing tribe would vote somebody out, but if they beat both tribes, they would vote two members back into the game and both tribes would vote somebody out. The Outcasts infamously won this challenge, sending both Drake and Morgan to Tribal Council.
In Survivor: Redemption Island, the challenge was used as the first ever Redemption Island duel. The castaways had to build a long pole out of sticks and rope. They would then use the pole to retrieve three keys hanging outside their cells. Once all the keys were retrieved, they had to unlock three padlocks on their cell doors, open the door, and walk through. Matt Elrod defeated Francesca Hogi in this challenge, eliminating her for good.
In Survivor: South Pacific the concept of the challenge was the same as in the season before it. This time it was used as the final pre-merge Redemption Island duel. Ozzy Lusth defeated Redemption Island champion, Christine Shields Markoski, re-entering the game and eliminating Christine.
In Survivor: Blood vs. Water, the challenge was be used as the duel between Katie Collins, Laura Morett, and Katie's mother, Tina Wesson. Tina gave advice to Katie in hopes of having her and Katie advance together. Unfortunately for the mother and daughter, Laura M. was able to continue her Redemption Island dominance and come in first. Katie initially had the lead, but when she dropped the second key in the sand, she was unable to get it out. This enabled Tina to catch and beat her daughter. Before opening the door and walking through, Tina asked Katie if she was alright with her doing it. Katie said she was alright with her mother advancing, which meant Katie was eliminated for good. Victory was bittersweet for Tina as Katie was permanently out of the game while she stayed on Redemption Island.
In Survivor: Cambodia, the challenge was incorporated as the final part of the Quest for Fire challenge, where contestants would have to retrieve a key to open the cell door and light their tribe's flame. Bayon defeated Ta Keo to win immunity, sending Ta Keo to Tribal Council with no time to strategize.
In Survivor: Edge of Extinction, the castaways from Edge of Extinction were first to climb atop a net crawl to retrieve a bag before going to their respective gates, where they would use sticking and string to build a pole to retrieve keys to unlock their cell door. After getting through the door, castaways would have to navigate a ball to the top a vertical snake maze, while standing on balance beam, from A Bridge You Must Cross. Rick Devens would ultimately win the challenge, and a spot back into the game.
Reappearing in Winners at War, the challenge was identical to the Edge of Extinction counterpart, once again being merged with A Bridge You Must Cross. Everyone except Amber Mariano, Parvati Shallow, and Yul Kwon purchased an advantage that allowed them to skip digging up their strings. Rob Mariano was the first to make it through the gate, although Tyson Apostol overtook him on the maze section, with Tyson just barely edging out the competition to sink his ball first, earning himself a spot back in the game.
| The Amazon|
| Pearl Islands|
"What the...? (Part 1)"
| Redemption Island|
"Keep Hope Alive"
| South Pacific|
| Blood vs. Water|
"Out on a Limb"
| Edge of Extinction|
"There's Always a Twist"
| Winners at War|
"This Is Where the Battle Begins"
- This challenge was used in all seasons to feature the Redemption Island twist: Redemption Island, South Pacific, and Blood vs. Water.
- In Pearl Islands, The Outcasts did not sit anyone out despite having an extra member. Despite having to rescue one extra person, they still won the challenge.
- The majority of the times this challenge has been used, it was fought by players trying to return into the game.
- It has been used as a Redemption Island duel in three of its uses, twice for the Edge of Extinction re-entry duel, and once as an Immunity Challenge featuring The Outcasts.